What to do First, High Value Questions

Clarity doesn’t require complexity. Sometimes three simple buckets — Now, Next, Later — reveal more about a team’s priorities, maturity, and value orientation than any polished roadmap ever could.

When I connect with a new team or org, one of the first things I do is ask for a simple NOW, NEXT, LATER view into the work they are doing.

Task lists or roadmaps are useful too, but I like the simplicity of three buckets for this altitude of making sense of things.

I ask several questions, but these four tell me a lot about the maturity of the team, the way they think about the work, the quick wins, the way they prioritize, the "value" of work, and their orientation to ambiguity and complexity - among other things.

This is how easy it is. Leaders, you can do this anytime, not just in your first 90 days.

If it’s a team our group it can drive interesting discussions, but works in one-on-one situations as well.

This is how it works.

Set the stage:

Base on everything going on and your view of the work and priorities, show me on the whiteboard (or miro digital whiteboard) what’s being worked on.

Don’t let them bog down on a spreadsheet, powerpoint, or roadmap they have. This is an organic view into their perspective while also helping you see the things that bubble up.

Where and how they share:

I typically suggest a post-it note in person or text box in miro with each thing being described in less than 10 words across one of three vertical columns.

1. The “Now” column (basically work in progress and this month)

2. The “Next” column (basically work to do after this – typically over 4-12 weeks)

3. The “Later” column (basically more than 3-6 months out)

An individual might put 3 to 10 items in each column. Obviously a group would multiply this number and likely introduce duplicates.

But its all good.

Here is what I’m looking for:

NOW - Is this work impactful? Is it valuable? To whom?

NEXT – is anything here more impactful to the business if we do it sooner instead of work that is currently in the NOW bucket? Why or why not?

LATER – Are these items confusing, ambiguous, or way too ambitious to be understood in a meaningful way? Are they clearly impactful or is their impact unclear?

And across all three categories I will ask:

1. Are we favoring comfort over doing the right-but-hard-thing?

2. Are we trying to do maintenance or value creation?

3. Are we too internally focused and not focused enough on the customer?

4. Are the things to big to complete in a reasonable time causing us to move to slowly?

In this way, 30 - 60 minutes of discussion can be very informing and also constructive.

The NOW/NEXT/LATER framework is a simple yet powerful tool for aligning teams and gaining insight into priorities. After doing this with several people or a group you should take time to reflect on what you learned.

Consider:

1. Where are the gaps or misalignments between individual and team perspectives? How might you address disconnects through open discussion?

2. Does the team have clarity on which initiatives truly drive impact aligned to company goals? Is this an area to better understand on how you got here and if refocusing is needed?

3. Is there a healthy balance of near-term execution and longer-term vision? Should you shift priorities if too heavily weighted in one direction? Is too much of the current work not actually impactful to the business or teams?

4. Is there an unhealthy emphasis on internal projects instead of customer value and growth?

5. Are dependencies across projects understood? Map out connections more to better understand.

6. Does the team feel empowered and accountable? Remove organizational obstacles.

From here, you can now lean into meaningful work based on relevant assessment of the work and current priorities.

What would happen if you did this today? Or this week? What would you discover? How would you codify it as an artifact and useful capture to leverage going forward?

#ThePathOfALeader
#GSD

Appreciate you,

Justin